메뉴 건너뛰기




Volumn 55, Issue 5, 2012, Pages 1978-1998

Discovery and synthesis of hydronaphthoquinones as novel proteasome inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID; CHYMOTRYPSIN; N [3 (1H TETRAZOL 5 YLTHIO) 4 HYDROXYNAPHTHALEN 1 YL) 4' (TRIFLUOROMETHYL)BIPHENYL 4 SULFONAMIDE; N [3 (1H TETRAZOL 5 YLTHIO) 4 HYDROXYNAPHTHALEN 1 YL] 4 CYCLO HEXYLBENZENESULFONAMIDE; N [3 (1H TETRAZOL 5 YLTHIO) 4 HYDROXYNAPHTHALEN 1 YL] 4' FLUOROBIPHENYL 4 SULFONAMIDE; N [3 (1H TETRAZOL 5 YLTHIO) 4 HYDROXYNAPHTHALEN 1 YL] 5 PHENYL THIOPHENE 2 SULFONAMIDE; N [3 (1H TETRAZOL 5 YLTHIO) 4 HYDROXYNAPHTHALEN 1 YL]BIPHENYL 4 SULFONAMIDE; PI 8182; PROTEASOME INHIBITOR; THIOGLYCOLIC ACID; THIOPHENE; UBIQUITINATED PROTEIN; UNCLASSIFIED DRUG;

EID: 84858010952     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm201118h     Document Type: Article
Times cited : (48)

References (39)
  • 1
    • 0842303313 scopus 로고    scopus 로고
    • Back to the future with ubiquitin
    • Pickart, C. M. Back to the future with ubiquitin Cell (Cambridge, MA, U.S.) 2004, 116, 181-190
    • (2004) Cell (Cambridge, MA, U.S.) , vol.116 , pp. 181-190
    • Pickart, C.M.1
  • 2
    • 25144466132 scopus 로고    scopus 로고
    • Intracellular protein degradation: From a vague idea, through the lysosome and the ubiquitin proteasome system, and onto human diseases and drug targeting (Nobel lecture)
    • Ciechanover, A. Intracellular protein degradation: from a vague idea, through the lysosome and the ubiquitin proteasome system, and onto human diseases and drug targeting (Nobel lecture) Angew. Chem., Int. Ed. 2005, 44, 5944-5967
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 5944-5967
    • Ciechanover, A.1
  • 3
    • 25144443718 scopus 로고    scopus 로고
    • The ubiquitin system for protein degradation and some of its roles in the control of the cell-division cycle (Nobel lecture)
    • Hershko, A. The ubiquitin system for protein degradation and some of its roles in the control of the cell-division cycle (Nobel lecture) Angew. Chem., Int. Ed. Engl. 2005, 44, 5932-5943
    • (2005) Angew. Chem., Int. Ed. Engl. , vol.44 , pp. 5932-5943
    • Hershko, A.1
  • 4
    • 84858047045 scopus 로고    scopus 로고
    • Ubiquitin at fox chase
    • Rose, I. Ubiquitin at fox chase Prix Nobel 2005, 218-225
    • (2005) Prix Nobel , pp. 218-225
    • Rose, I.1
  • 6
    • 0032539909 scopus 로고    scopus 로고
    • The ubiquitin-proteasome pathway: The complexity and myriad functions of proteins death
    • Ciechanover, A.; Schwartz, A. L. The ubiquitin-proteasome pathway: the complexity and myriad functions of proteins death Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 2727-2730
    • (1998) Proc. Natl. Acad. Sci. U.S.A. , vol.95 , pp. 2727-2730
    • Ciechanover, A.1    Schwartz, A.L.2
  • 7
    • 0036139950 scopus 로고    scopus 로고
    • Ubiquitin-mediated degradation of cellular proteins in health and disease
    • Ciechanover, A.; Schwartz Alan, L. Ubiquitin-mediated degradation of cellular proteins in health and disease Hepatology 2002, 35, 3-6
    • (2002) Hepatology , vol.35 , pp. 3-6
    • Ciechanover, A.1    Schwartz Alan, L.2
  • 9
    • 2342667387 scopus 로고    scopus 로고
    • The development of proteasome inhibitors as anticancer drugs
    • Adams, J. The development of proteasome inhibitors as anticancer drugs Cancer Cell 2004, 5, 417-421
    • (2004) Cancer Cell , vol.5 , pp. 417-421
    • Adams, J.1
  • 11
    • 13844320703 scopus 로고    scopus 로고
    • Proteasome inhibition in multiple myeloma: Therapeutic implication
    • 2 plates.
    • Chauhan, D.; Hideshima, T.; Anderson, K. C. Proteasome inhibition in multiple myeloma: therapeutic implication Annu. Rev. Pharmacol. Toxicol. 2005, 45, 465-476 2 plates.
    • (2005) Annu. Rev. Pharmacol. Toxicol. , vol.45 , pp. 465-476
    • Chauhan, D.1    Hideshima, T.2    Anderson, K.C.3
  • 14
    • 34250011799 scopus 로고    scopus 로고
    • The ubiquitin-proteasome system and its role in inflammatory and autoimmune diseases
    • Wang, J.; Maldonado, M. A. The ubiquitin-proteasome system and its role in inflammatory and autoimmune diseases Cell. Mol. Immunol. 2006, 3, 255-261
    • (2006) Cell. Mol. Immunol. , vol.3 , pp. 255-261
    • Wang, J.1    Maldonado, M.A.2
  • 15
    • 0033564512 scopus 로고    scopus 로고
    • Eponemycin exerts its antitumor effect through the inhibition of proteasome function
    • Meng, L.; Kwok, B. H.; Sin, N.; Crews, C. M. Eponemycin exerts its antitumor effect through the inhibition of proteasome function Cancer Res. 1999, 59, 2798-2801
    • (1999) Cancer Res. , vol.59 , pp. 2798-2801
    • Meng, L.1    Kwok, B.H.2    Sin, N.3    Crews, C.M.4
  • 16
    • 0343262654 scopus 로고    scopus 로고
    • Crystal structure of epoxomicin:20S proteasome reveals a molecular basis for selectivity of a′,b′-epoxyketone proteasome inhibitors
    • Groll, M.; Kim, K. B.; Kairies, N.; Huber, R.; Crews, C. M. Crystal structure of epoxomicin:20S proteasome reveals a molecular basis for selectivity of a′,b′-epoxyketone proteasome inhibitors J. Am. Chem. Soc. 2000, 122, 1237-1238
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 1237-1238
    • Groll, M.1    Kim, K.B.2    Kairies, N.3    Huber, R.4    Crews, C.M.5
  • 17
    • 69949108710 scopus 로고    scopus 로고
    • Snapshots of the fluorosalinosporamide/20S complex offer mechanistic insights for fine tuning proteasome inhibition
    • Groll, M.; McArthur Katherine, A.; Macherla Venkat, R.; Manam Rama, R.; Potts Barbara, C. Snapshots of the fluorosalinosporamide/20S complex offer mechanistic insights for fine tuning proteasome inhibition J. Med. Chem. 2009, 52, 5420-5428
    • (2009) J. Med. Chem. , vol.52 , pp. 5420-5428
    • Groll, M.1    McArthur Katherine, A.2    MacHerla Venkat, R.3    Manam Rama, R.4    Potts Barbara, C.5
  • 18
    • 0034864799 scopus 로고    scopus 로고
    • Proteasome inhibitors: From research tools to drug candidates
    • Kisselev, A. F.; Goldberg, A. L. Proteasome inhibitors: from research tools to drug candidates Chem. Biol. 2001, 8, 739-758
    • (2001) Chem. Biol. , vol.8 , pp. 739-758
    • Kisselev, A.F.1    Goldberg, A.L.2
  • 20
    • 84858023215 scopus 로고    scopus 로고
    • Proteasome inhibition as a therapeutic strategy in patients with multiple myeloma
    • Fuchs, O. Proteasome inhibition as a therapeutic strategy in patients with multiple myeloma Mult. Myeloma 2009, 101-125
    • (2009) Mult. Myeloma , pp. 101-125
    • Fuchs, O.1
  • 26
    • 0000107112 scopus 로고
    • Chlorination of N -arylsulfonyl-1,4-aminonaphthols and N -arylsulfonyl-1,4-naphthoquinone-1,4-imines
    • Avdeenko, A. P.; Velichko, N. V.; Romanenko, E. A.; Pirozhenko, V. V. Chlorination of N -arylsulfonyl-1,4-aminonaphthols and N -arylsulfonyl-1,4- naphthoquinone-1,4-imines Zh. Org. Khim. 1991, 27, 1747-1757
    • (1991) Zh. Org. Khim. , vol.27 , pp. 1747-1757
    • Avdeenko, A.P.1    Velichko, N.V.2    Romanenko, E.A.3    Pirozhenko, V.V.4
  • 27
    • 33845377922 scopus 로고
    • 1,4-Addition of triazolium thiolates to quinones
    • Altland, H. W.; Briffa, B. F., Jr. 1,4-Addition of triazolium thiolates to quinones J. Org. Chem. 1985, 50, 433-437
    • (1985) J. Org. Chem. , vol.50 , pp. 433-437
    • Altland, H.W.1    Briffa Jr., B.F.2
  • 29
    • 0345948640 scopus 로고
    • Reaction of N -(arylsulfonyl)- p -naphthoquinonimines with acylhydrazines
    • Avdeenko, A. P.; Evgrafova, N. I. Reaction of N -(arylsulfonyl)- p -naphthoquinonimines with acylhydrazines Zh. Org. Khim. 1987, 23, 1060-1063
    • (1987) Zh. Org. Khim. , vol.23 , pp. 1060-1063
    • Avdeenko, A.P.1    Evgrafova, N.I.2
  • 30
    • 84936350638 scopus 로고
    • Reactions of benzo analogs of N -phenyl-1,4-benzoquinone monoimine with thiols
    • Thiols; Coj, E.; Afanas'eva, G. B.; Chupakhin, O. N.; Sidorov, E. O. Reactions of benzo analogs of N -phenyl-1,4-benzoquinone monoimine with thiols Zh. Org. Khim. 1989, 25, 2409-2416
    • (1989) Zh. Org. Khim. , vol.25 , pp. 2409-2416
    • Thiols1    Coj, E.2    Afanas'Eva, G.B.3    Chupakhin, O.N.4    Sidorov, E.O.5
  • 31
    • 0038328613 scopus 로고
    • Reduction of quinones and quinonemonosulfonimides with N, N -diethylhydroxylamine
    • Fujita, S.; Sano, K. Reduction of quinones and quinonemonosulfonimides with N, N -diethylhydroxylamine J. Org. Chem. 1979, 44, 2647-2651
    • (1979) J. Org. Chem. , vol.44 , pp. 2647-2651
    • Fujita, S.1    Sano, K.2
  • 32
    • 0036579887 scopus 로고    scopus 로고
    • Synthesis of 2-alkoxy 1,4-naphthoquinone derivatives as antiplatelet, antiinflammatory, and antiallergic agents
    • Lien, J.-C.; Huang, L.-J.; Teng, C.-M.; Wang, J.-P.; Kuo, S.-C. Synthesis of 2-alkoxy 1,4-naphthoquinone derivatives as antiplatelet, antiinflammatory, and antiallergic agents Chem. Pharm. Bull. 2002, 50, 672-674
    • (2002) Chem. Pharm. Bull. , vol.50 , pp. 672-674
    • Lien, J.-C.1    Huang, L.-J.2    Teng, C.-M.3    Wang, J.-P.4    Kuo, S.-C.5
  • 33
    • 84858024741 scopus 로고
    • Studies in the heterocyclic compounds. II. The mass spectra of some thiophene-sulfonyl derivatives
    • Obafemi, C. A. Studies in the heterocyclic compounds. II. The mass spectra of some thiophene-sulfonyl derivatives Phosphorus Sulfur 1980, 8, 201-204
    • (1980) Phosphorus Sulfur , vol.8 , pp. 201-204
    • Obafemi, C.A.1
  • 34
    • 34250869591 scopus 로고    scopus 로고
    • Enesulfonamides as nucleophiles in catalytic asymmetric reactions
    • Matsubara, R.; Doko, T.; Uetake, R.; Kobayashi, S. Enesulfonamides as nucleophiles in catalytic asymmetric reactions Angew. Chem., Int. Ed. 2007, 46, 3047-3050
    • (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 3047-3050
    • Matsubara, R.1    Doko, T.2    Uetake, R.3    Kobayashi, S.4
  • 35
    • 0000012463 scopus 로고
    • Quinone imides. XXXIX. Adducts of quinone monoimides and conversion of active methylene adducts to benzofurans
    • Adams, R.; Whitaker, L. Quinone imides. XXXIX. Adducts of quinone monoimides and conversion of active methylene adducts to benzofurans J. Am. Chem. Soc. 1956, 78, 658-663
    • (1956) J. Am. Chem. Soc. , vol.78 , pp. 658-663
    • Adams, R.1    Whitaker, L.2
  • 37
    • 33845377922 scopus 로고
    • 1,4-Addition of triazolium thiolates to quinones
    • Altland, H. W.; Briffa, B. F., Jr. 1,4-Addition of triazolium thiolates to quinones J. Org. Chem. 1985, 50, 433-437
    • (1985) J. Org. Chem. , vol.50 , pp. 433-437
    • Altland, H.W.1    Briffa Jr., B.F.2
  • 38
    • 0028822833 scopus 로고
    • Angiotensin receptor antagonists: Focus on losartan
    • Johnston, C. I. Angiotensin receptor antagonists: focus on losartan Lancet 1995, 346, 1403-1407
    • (1995) Lancet , vol.346 , pp. 1403-1407
    • Johnston, C.I.1
  • 39
    • 7744243992 scopus 로고    scopus 로고
    • Bioisosterism: A rational approach in drug design
    • Patani, G. A.; LaVoie, E. J. Bioisosterism: A rational approach in drug design Chem. Rev. 1996, 96, 3147-3176
    • (1996) Chem. Rev. , vol.96 , pp. 3147-3176
    • Patani, G.A.1    Lavoie, E.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.